It’s kind of mind-blowing to realize that Leonard DiCaprio has been nominated for 167 awards over the course of his career, and he’s taken home 50 of them. And a lot of those are really impressive, including the 2016 Academy Award in the category of Best Actor (The Revenant), three Best Actor Golden Globe Awards (The Aviator, The Wolf of Wall Street, and The Revenant), four MTV Movie Awards (Titanic, The Aviator, The Wolf of Wall Street, and The Revenant) and three Teen Choice Awards (Catch Me If You Can, Shutter Island, and The Revenant).

It just seems impossible for a guy who was considered a child star, a pin-up idol in teen magazines around the world, to have come that far, because that’s just not something that normally happened. Then again, going against convention is something that has defined Leo’s career from the very beginning.

Born Nov.11, 1974, Leo began his career at the age of 14, landing a commercial for Matchbox cars. Two years later he became part of the cast of the TV show Parenthood, based on the film of the same name, and from there he spent some time on the soap opera Santa Barbara. What truly changed things up for him, though, was when he was cast in the role of homeless kid Luke Brower, who is brought into the Seaver household in the final season of the ABC sitcom Growing Pains. Although the show was far from overly serious, Leo was able to bring something special to the role of Luke that allowed him to stand out from a lot of other kids on television at the time.

Things really began heating up shortly after the show ended, with Robert De Niro actually choosing him to star in This Boy’s Life, which gained him critical acclaim and led to films like What’s Eating Gilbert Grape, with things moved forward from there. Of course, in 1997 he co-starred with Kate Winslet in James Cameron’s Titanic and that changed absolutely everything for him.

Leo once explained just why he and Kate decided to do the film and what they felt it could do for their careers. “Titanic was very much an experiment for Kate Winslet and I,” he said. “We’d done all of these independent movies and I used [my fame from the film] as a blessing, to make R-rated, different kinds of movies. To throw the dice a little bit on things I wanted to act in.”

Check out the gallery for a guide to Leo’s films!